Pyrazinyl and pyridinyl bis-azomethines formation: an experimental and computational study

被引：1

作者：

Coufal, Radek ^{[1
]}

Vohlidal, Jiri ^{[2
]}

机构：

[1] Tech Univ Liberec, Fac Hlth Studies, Dept Sci & Res, Studentska 1402-2,Liberec 1, Liberec 46117, Czech Republic

[2] Charles Univ Prague, Dept Phys & Macromol Chem, Fac Sci, Hlavova 8-2030, Prague 12840 2, Czech Republic

来源：

SCIENTIFIC REPORTS | 2023年 / 13卷 / 01期

关键词：

CRYSTAL-STRUCTURE; SCHIFF-BASES; COMPLEXES; STABILIZATION; CONDENSATION; CHEMISTRY; MECHANISM; COPPER(I); CAVITAND; LIGANDS;

D O I：

10.1038/s41598-023-44585-7

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Formation of bis-azomethines from hydrazine and heterocyclic aromatic carbaldehydes, namely pyridine-2-carbaldehyde and pyrazine-2-carbaldehyde, is studied using density functional theory. The theoretical investigation is correlated with experimental results obtained by means of NMR spectroscopy. The presence of bis-hemiaminal intermediates is evidenced by NMR spectra while surprisingly stable hemiaminal intermediate was isolated experimentally. Water, methanol and acetic acid were outlined to play a crucial role as active catalysts of elementary steps of the reaction mechanisms. The possible reaction sequences, i.e. addition-dehydration-addition-dehydration or addition-addition-dehydration-dehydration are investigated and discussed. Also, alternative mechanistic path via ionic mechanism was proposed for the formation of hemiaminals.

引用

页数：12

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